CA2294147C - Process for the production of methyl methacrylate - Google Patents
Process for the production of methyl methacrylate Download PDFInfo
- Publication number
- CA2294147C CA2294147C CA002294147A CA2294147A CA2294147C CA 2294147 C CA2294147 C CA 2294147C CA 002294147 A CA002294147 A CA 002294147A CA 2294147 A CA2294147 A CA 2294147A CA 2294147 C CA2294147 C CA 2294147C
- Authority
- CA
- Canada
- Prior art keywords
- methyl methacrylate
- crystals
- product stream
- liquid
- mother liquor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 title claims abstract description 65
- 238000000034 method Methods 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- 239000012535 impurity Substances 0.000 claims abstract description 25
- 238000001640 fractional crystallisation Methods 0.000 claims abstract description 9
- 239000013078 crystal Substances 0.000 claims description 41
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 25
- 239000012263 liquid product Substances 0.000 claims description 23
- 239000007788 liquid Substances 0.000 claims description 20
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 18
- 239000012452 mother liquor Substances 0.000 claims description 18
- 238000002844 melting Methods 0.000 claims description 13
- 230000008018 melting Effects 0.000 claims description 13
- 238000001816 cooling Methods 0.000 claims description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 11
- 238000002425 crystallisation Methods 0.000 claims description 10
- 238000006482 condensation reaction Methods 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 6
- 235000019260 propionic acid Nutrition 0.000 claims description 6
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 6
- 239000000155 melt Substances 0.000 claims description 5
- 239000002243 precursor Substances 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 2
- 230000008014 freezing Effects 0.000 abstract 1
- 238000007710 freezing Methods 0.000 abstract 1
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 24
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 3
- 229940017219 methyl propionate Drugs 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229920006243 acrylic copolymer Polymers 0.000 description 1
- 150000001351 alkyl iodides Chemical class 0.000 description 1
- -1 alkyl methacrylates Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9714632.8 | 1997-07-12 | ||
| GBGB9714632.8A GB9714632D0 (en) | 1997-07-12 | 1997-07-12 | Process for the production of methyl methacrylate |
| PCT/GB1998/002028 WO1999002481A1 (en) | 1997-07-12 | 1998-07-10 | Process for the production of methyl methacrylate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2294147A1 CA2294147A1 (en) | 1999-01-21 |
| CA2294147C true CA2294147C (en) | 2007-02-13 |
Family
ID=10815711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002294147A Expired - Fee Related CA2294147C (en) | 1997-07-12 | 1998-07-10 | Process for the production of methyl methacrylate |
Country Status (22)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4033329B2 (ja) * | 2002-01-23 | 2008-01-16 | 三菱レイヨン株式会社 | 注型成型品の製造方法および注型成型品 |
| EP2025660A3 (en) * | 2007-08-14 | 2009-03-04 | Rohm and Haas Company | Processes for producing ethylene and carbon monoxide mixtures from ethane |
| GB0809332D0 (en) * | 2008-05-22 | 2008-07-02 | Lucite Int Uk Ltd | Production of ethylenically unsaturated acids or esters thereof |
| CN102471214B (zh) * | 2009-06-30 | 2014-10-01 | 株式会社日本触媒 | 丙烯酸的析晶装置及使用其的丙烯酸的析晶方法 |
| US8883672B2 (en) | 2011-09-16 | 2014-11-11 | Eastman Chemical Company | Process for preparing modified V-Ti-P catalysts for synthesis of 2,3-unsaturated carboxylic acids |
| US8993801B2 (en) | 2011-09-16 | 2015-03-31 | Eastman Chemical Company | Process for preparing V-Ti-P catalysts for synthesis of 2,3-unsaturated carboxylic acids |
| US9573119B2 (en) | 2011-09-16 | 2017-02-21 | Eastman Chemical Company | Process for preparing V—Ti—P catalysts for synthesis of 2,3-unsaturated carboxylic acids |
| US8765629B2 (en) | 2011-09-16 | 2014-07-01 | Eastman Chemical Company | Process for preparing V-Ti-P catalysts for synthesis of 2,3-unsaturated carboxylic acids |
| CN115959994A (zh) * | 2021-10-13 | 2023-04-14 | 上海浦景化工技术股份有限公司 | 一种制备高纯度mma的系统及方法 |
| GB202118029D0 (en) | 2021-12-13 | 2022-01-26 | Mitsubishi Chemical Uk Ltd | A process for purification of crude methyl methacrylate |
| EP4321500A1 (en) * | 2022-08-08 | 2024-02-14 | Arkema France | Method and installation for the production of a monomer by depolymerization of the corresponding polymer |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1107234A (en) * | 1965-10-22 | 1968-03-27 | Air Reduction | Production of acrylate and methacrylate esters |
| US3440276A (en) * | 1965-12-29 | 1969-04-22 | Commercial Solvents Corp | Process for preparing acrylic esters |
| US3535371A (en) * | 1965-12-29 | 1970-10-20 | Commercial Solvents Corp | Process for the preparation of acrylic esters |
| UST955005I4 (en) * | 1967-12-26 | 1977-02-01 | Process for purification of alkyl methacrylates | |
| FR1598545A (enrdf_load_stackoverflow) | 1967-12-26 | 1970-07-06 | ||
| DE2612843B2 (de) * | 1976-03-26 | 1979-10-31 | Dynamit Nobel Ag, 5210 Troisdorf | Bis-acrylester und Bis-methacrylester, Verfahren zur Herstellung dieser Verbindungen und deren Verwendung |
| US4230888A (en) * | 1977-12-15 | 1980-10-28 | Standard Oil Company (Ohio) | Process for purification of acrylic acid by fractional crystallization |
| TW305830B (enrdf_load_stackoverflow) * | 1993-03-26 | 1997-05-21 | Sulzer Chemtech Ag | |
| JP3293702B2 (ja) * | 1993-11-09 | 2002-06-17 | 三菱瓦斯化学株式会社 | メチルメタクリレート系重合体の製造方法 |
| FR2720749B1 (fr) * | 1994-06-06 | 1996-07-19 | Atochem Elf Sa | Procédé de fabrication d'un poly(méthacrylate de méthyle) à teneur élevée en triades syndiotactiques. |
| KR960000850A (ko) * | 1994-06-06 | 1996-01-25 | 사토 아키오 | 메타크릴산메틸의 연속제조방법 |
| MY120051A (en) * | 1997-07-30 | 2005-08-30 | Mitsubishi Rayon Co | Process for purification of (meth)acrylic acid |
| EP1078669A1 (de) * | 1999-08-23 | 2001-02-28 | Sulzer Chemtech AG | Verfahren und Kristallisator zur Reinigung von Stoffen oder Stoffgemischen |
| DE10003497A1 (de) * | 2000-01-27 | 2001-04-12 | Basf Ag | Reinigungsverfahren für (Meth)acrylsäure |
-
1997
- 1997-07-12 GB GBGB9714632.8A patent/GB9714632D0/en active Pending
-
1998
- 1998-07-10 AU AU82344/98A patent/AU729645B2/en not_active Ceased
- 1998-07-10 AT AT98932415T patent/ATE233725T1/de not_active IP Right Cessation
- 1998-07-10 NZ NZ501882A patent/NZ501882A/en unknown
- 1998-07-10 HU HU0002515A patent/HUP0002515A3/hu unknown
- 1998-07-10 WO PCT/GB1998/002028 patent/WO1999002481A1/en active IP Right Grant
- 1998-07-10 MY MYPI98003175A patent/MY120750A/en unknown
- 1998-07-10 PL PL337995A patent/PL197704B1/pl not_active IP Right Cessation
- 1998-07-10 US US09/462,669 patent/US6670501B1/en not_active Expired - Fee Related
- 1998-07-10 ES ES98932415T patent/ES2192776T3/es not_active Expired - Lifetime
- 1998-07-10 KR KR1020007000272A patent/KR100547072B1/ko not_active Expired - Fee Related
- 1998-07-10 CZ CZ20000079A patent/CZ296332B6/cs not_active IP Right Cessation
- 1998-07-10 CA CA002294147A patent/CA2294147C/en not_active Expired - Fee Related
- 1998-07-10 ZA ZA986166A patent/ZA986166B/xx unknown
- 1998-07-10 JP JP2000502011A patent/JP4343423B2/ja not_active Expired - Fee Related
- 1998-07-10 EP EP98932415A patent/EP0996611B1/en not_active Expired - Lifetime
- 1998-07-10 RU RU2000103271/04A patent/RU2207334C2/ru not_active IP Right Cessation
- 1998-07-10 BR BR9810705-4A patent/BR9810705A/pt not_active Application Discontinuation
- 1998-07-10 ID IDW20000055D patent/ID24501A/id unknown
- 1998-07-10 DE DE69811899T patent/DE69811899T2/de not_active Expired - Lifetime
- 1998-07-10 CN CN98807128A patent/CN1130331C/zh not_active Expired - Fee Related
- 1998-07-16 TW TW087111574A patent/TW561147B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0002515A2 (hu) | 2000-11-28 |
| EP0996611A1 (en) | 2000-05-03 |
| PL197704B1 (pl) | 2008-04-30 |
| CA2294147A1 (en) | 1999-01-21 |
| KR20010021713A (ko) | 2001-03-15 |
| DE69811899D1 (de) | 2003-04-10 |
| MY120750A (en) | 2005-11-30 |
| KR100547072B1 (ko) | 2006-02-01 |
| GB9714632D0 (en) | 1997-09-17 |
| WO1999002481A1 (en) | 1999-01-21 |
| HUP0002515A3 (en) | 2006-02-28 |
| ID24501A (id) | 2000-07-20 |
| NZ501882A (en) | 2001-09-28 |
| DE69811899T2 (de) | 2003-11-06 |
| US6670501B1 (en) | 2003-12-30 |
| AU729645B2 (en) | 2001-02-08 |
| AU8234498A (en) | 1999-02-08 |
| CZ200079A3 (cs) | 2000-05-17 |
| RU2207334C2 (ru) | 2003-06-27 |
| ZA986166B (en) | 1999-01-22 |
| TW561147B (en) | 2003-11-11 |
| PL337995A1 (en) | 2000-09-25 |
| ATE233725T1 (de) | 2003-03-15 |
| CN1263521A (zh) | 2000-08-16 |
| JP4343423B2 (ja) | 2009-10-14 |
| CN1130331C (zh) | 2003-12-10 |
| BR9810705A (pt) | 2000-08-08 |
| ES2192776T3 (es) | 2003-10-16 |
| JP2001509499A (ja) | 2001-07-24 |
| CZ296332B6 (cs) | 2006-02-15 |
| EP0996611B1 (en) | 2003-03-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |